1-Phenylcyclopropanecarbonitrile → 1-Phenylcyclopropanemethanamine

HRID 74747노트

반응식

HRID 74747 반응식
[C:1]1([C:7]2([C:10]#[N:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2([CH2:10][NH2:11])[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 702881-PhenylcyclopropanecarbonitrileHCID 21226445Aluminium lithium hydride

생성물 1

HCID 702871-Phenylcyclopropanemethanamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 1-phenylcyclopropanecarbonitrile (50 g, 0.34 mol, 1 eq.) in tetrahydrofuran (500 mL, 0.7 M) at 0° C. was added lithium aluminum hydride (23 g, 0.35 mol, 1.03 eq.). The reaction mixture was stirred at 0° C. for one hour and then at reflux for one hour. The reaction mixture was then cooled down and quenched with water (23 mL) and a 15% aqueous sodium hydroxide solution (69 mL). The mixture was filtered and concentrated in vacuo to afford #*1 (36 g, 72%). LC-MS: m/z 148.1 [M+H+], retention time=0.86 minutes; 1H NMR (400 MHz, CDCl3) δ 7.2-7.4 (m, 5H), 2.78 (s, 2H), 1.19 (br s, 2H), 0.72-0.84 (m, 4H).

후처리

  1. temperatureat reflux for one hour
  2. temperatureThe reaction mixture was then cooled down
  3. customquenched with water (23 mL)
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customto afford #*1 (36 g, 72%)

출처 및 근거

ORD 기록
ord-38f440307c9f4c8baf1bb6fa411de794
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828401B2

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